1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22277820, compound

HRID 2055319Notes

Reaction equation

HRID 2055319 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[C:3]=1[CH3:15].CCN=C=NCCCN(C)C.[O:27]1[CH2:31][CH2:30][CH:29]([C:32](O)=[O:33])[CH2:28]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:15][C:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:13]=[CH:14][C:2]=1[NH:1][C:32]([CH:29]1[CH2:30][CH2:31][O:27][CH2:28]1)=[O:33]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 22277806HCID 22277806, compound

Product 1

HCID 22277820HCID 22277820, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Amino-1-methyldibenzothiophene (Method 10; 0.337 g, 1.58 mmol), 4-(dimethylamino)pyridine (0.213 g, 1.74 mmol), EDAC (0.334 g, 1.74 mmol) and tetrahydro-3-furoic acid (0.167 ml, 1.74 mmol) were stirred in DCM (20 ml) at reflux under an argon atmosphere for 64 h. The product was purified by flash chromatography eluting with DCM—5% methanol/DCM. Evaporation of the appropriate fractions gave the product as a white solid. NMR: 9.77 (brs, 1H), 8.44 (m, 1H), 8.04 (m, 1H), 7.82 (d, 1H), 7.52 (m, 2H), 7.36 (d, 1H), 4.00 (m, 1H), 3.76 (m, 3H), 3.27 (m, 1H), 2.68 (s, 3H), 2.15 (q, 2H); m/z 313.

Workup

  1. temperatureat reflux under an argon atmosphere for 64 h
  2. customThe product was purified by flash chromatography
  3. washeluting with DCM—5% methanol/DCM
  4. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-1bf88e778bd6450ca8cb29ac692341a5
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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